BETAINES 45 



chloride, from which it is separated by its greater solubility in water ; 

 yield 5*5 grm. per kilo, of air dry Herba Betonicce. 



In a later paper Schulze and Trier [1912, 2, section on betaine] 

 state that another substance of the formula C 7 H 13 O 3 N is also present. 

 Kiing and Trier [1913] have shown that the latter base is dextro- 

 rotatory and have named it turicine. It is the enantiomorph of 

 betonicine, which is laevo-rotatory. Kiing [1913] obtained both these 

 bases by methylation of oxyproline from gelatin, so that they have the 

 following constitution : 



H 

 \C CH 2 



HO/ | | H 



H 2 C C-C : O 



\/ I 



N O 



/ \ 

 CH 3 CH 3 



Trimethylhistidine, C 9 H 15 O 2 N 3 . 



A base of the above composition was isolated by Kutscher [1910, 4] 

 from the lysine fraction of a commercial mushroom extract and after- 

 wards named hercynine. The base gave an intense red coloration 

 with sodium p-diazobenzene sulphonate, but neither Millon's reaction 

 nor any reaction for tryptophane. Only the aurichloride was prepared 

 and of this the melting point was not given. Kutscher considered 

 that the base was probably a trimethylhistidine and later Engeland 

 and Kutscher [1912, I] showed its identity with the synthetic betaine 

 obtained from a-chloro-/3-iminazolyl-propionic acid and trimethyl- 

 amine. The constitution is therefore 



CH-NH> 



The same base was obtained more recently by Reuter [1912, Ch. I] 

 from the arginine fraction of Boletus edulis (8 grm. of the monopicrate 

 from 2| kilos, of the dried fungus), and Barger and Ewins [1913] have 

 shown that it is also formed by the oxidation of ergothioneine (see 

 next section). The direct methylation of histidine with dimethyl- 

 sulphate leads to the formation of a pentamethyl derivative, since the 

 imino-group of the glyoxaline ring is also attacked (Engeland and 

 Kutscher [1912, 2]). 



